Water → HCID 66696592, compound

Participants

Reaction Steps

A mixture of 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.67 g, 7.97 mmol), 4-bromo-3-fluorobenzaldehyde (1.62 g, 7.97 mmol), and K2CO3 (2.20 g, 15.9 mmol) in MeOH (40 mL) was heated to reflux. After 1.5 hr additional 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (106 mg, 0.51 mmol) was added and the reaction mixture was again heated at reflux for 1.5 hr. The reaction was cooled to ambient temperature, water (200 mL) was added and the product was extracted with EtOAc (200 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF25-40G column, 0%-30% EtOAc/hexanes, 30 mL/min), which yielded 1.86 g (91%) of the title compound as an orange solid. 1H NMR (300 MHz, CH3OH-d4) δ 8.18 (s, 1H), 7.73 (dd, J=8.4, 7.3 1H), 7.49 (dd, J=9.9, 2.0 1H), 7.41 (dd, J=8.3, 1.8 1H), 2.42 (s, 3H). MS (DCI+) m/z 256/258 (M+H).

Provenance & Evidence